"Why I'm cheating on my wife of five years with multiple women"

Dylan*, a 33-year-old policy advisor from London, has been using the extra-marital affairs site Ashley Madison to cheat on his wife since 2014. They got together 10 years ago when they were 23, and have been married for five years.

In 2017, 70% of Ashley Madison's new UK members were male and aged 35 and under. The most common reason they cited for joining the site was that the sex in their current relationship was "rare" or "non-existent". Dylan tells Cosmopolitan UK why there's "something quite satisfying" about his "secret life".

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"I had my first 'fling' about three years ago. It was after one of those interesting work dos and we'd all had a little bit to drink. This very attractive senior member of staff was being very seductive. She was like, 'Oh there's no one else in the building.' I guess I was led astray a little. It was Christmas, which I know sounds very cliché but it's how it happened. Obviously I felt guilty, but it was incredible at the same time.

After that initial little fling with my colleague, something just clicked at home. The next time I was having sex with my wife Jenny*, it was amazing. While our sex had been great to begin with, things had mellowed out and we became a bit sexually incompatible. I'm always very attentive and am vocal and communicative about our sex life and what things we could try. But she's a very strong woman, so will be like, 'No, I don't want to do that.' And that's fine.

On this occasion though, our sex just felt very primal and selfish. Afterwards, she just said, 'wow'. And I told her it was probably so great because we hadn't seen each other in a while. But I think maybe it was driven by a little bit of guilt on my part. At the same time, I was so turned on thinking about what I'd done. It was this double edged sword - while the fling had made me feel guilty, it had also been horrifically erotic.

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A little while after that, Jenny and I weren't really seeing that much of each other, this was mainly due to work commitments. We're both very independent anyway, but it was like we were like ships passing in the dark.

Where it all began

I saw a pop up advert for Ashley Madison. I planned to see what it was all about and didn’t really intend to do anything. But a few days later I found myself feeling more and more intrigued. 'What happens here?' I wondered. 'What does it involve?’ I hadn’t been searching for an affair because it’s not like I’m in a terrible marriage. Jenny and I talk a lot and we’re each other’s best friends, blah blah blah. I’m extremely happy with her in a lot of senses and I definitely love her. However, while we’re as close as any married couple, there’s an absence of what I would describe as a 'healthy sexual relationship'.

So I signed up and bought 100 credits, which cost somewhere between £50 and £100 and allows you to message other members. I've probably paid that three times a year for the last three years.

It would be disingenuous to say it's not about attractiveness when looking for someone to have a fling with. But for me, it’s become much more about sexual freedom and liberty. I wouldn't be interested in meeting someone who just wanted to have straight sex in a hotel room. So, I’ll discuss my kinks before we meet up. I’m not looking for somebody who I can potentially spend the rest of my life with, or even the weekend with. It’s about having a fun evening or afternoon and then leaving it a couple of weeks or a month before meeting up again.

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Keeping the secret

I'll start off by chatting with them on the website a bit, then shifting to other chat apps. The first rule is just don’t keep anything on your phone. It can be tiresome to keep deleting things - I delete things off my phone at the end of every day - but you’ve got to make sure you have a number of firewalls to control what's easily accessible on your phone. I have a chat on an online platform that’s not on my phone, so a woman's message couldn't just pop up on my home screen. While I've nearly made a mistake a few times because I became too relaxed, I just said to myself, 'You don't need to stop entirely but you do need to be more careful.'

In the nicest possible way, I’m not going to pay someone's rent or buy them shoes.

Since I joined three years ago, I've probably had sex with about five women. While there's been a couple of others (it's not progressed very far after having an initial drink), I've been with a few really lovely women for a number of months. My preference is that the women I meet are also married. I need that mutually assured destruction - it’s important to me that the woman is risking the same and isn’t going to get irritated if I’m not able to contact them for a while. There’s a more inherent understanding of what you can and can’t do when the other person's married.

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One fling was for eight months, although it wasn’t every week during that time... it drifted in and out and went through various stages of intensity. Then, she developed feelings that were going beyond what I was comfortable with. I’d said from the start what I was looking for. In the nicest possible way, I’m not going to pay someone's rent or buy them shoes. In this case, we were getting too involved with each other and needed to draw a line under it. It felt like the right moment to stop.

Sometimes I’ve realised the person I'm seeing isn't as much of a match as I thought they were. You can often see the jealousy start to rise in people, they want to know what you're doing or why you're still on the site. I don’t need that kind of hassle, I have no incentive to manage it. There's also been a couple of one night stands. I've got that out of my system, itched that scratch as it were.

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It’s almost like taking a drug because you have that initial high that you’re constantly trying to get back to. Meeting someone new, discovering something about them, the anticipation and nervousness, the adrenaline when you go to meet them, the sex and living out what you were talking about doing to each other. That’s really quite exciting.

Being careful

While I'll meet someone wherever’s convenient, it also has to be suitable - where there aren’t going to be people you might know. I don’t entertain the idea of bringing people back to mine and Jenny's place, but other women have because their husbands are away for periods of time and they have a free house.

I haven’t had an STI test since... I think clearly I should, but I haven't.

It’s not uncommon for me to have 'work functions' in the evening. Or, if it’s in the day, I can slip out and say I’m going to an external meeting. I’ve done an overnight thing a couple of times but as it isn't a common part of my job or normal behaviour, I have to be really careful. Often, I'll go for a drink with a woman in the evening and say I'm with colleagues. Jenny's never been suspicious. I’ve always been consistent - I’m not going to say I'm with one of my best friends and then have them post on Facebook they’re having a lovely time somewhere without me.

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I’m careful to use protection with everybody, but there was one woman who that was just her ‘thing’ [not to use condoms]. That was an interesting one. She was slightly older and on top so I couldn’t escape. She had me pinned down and afterwards was like, ‘Don’t worry, I’ll sort it out’. She text me the next day saying she got the morning after pill. It was one of those signs - I couldn’t see her again. That was the only time I’ve not used condoms. I haven’t had an STI test since... I think clearly I should, but I haven't.

Coming clean

Do I think I’ll ever tell Jenny the truth? No, is the short answer. I do keep on wondering if I've exhausted this now... whether I can stop or if I need to get some proper counselling and sort it out. To have a relationship with someone you love and to go and do this is pretty terrible by any kind of measure. How do I continue to do that behaviour? It’s clearly something that needs looking at more. Later, I might go and talk to someone about it, but at the moment it’s fun.

I’ve asked my wife a couple of times, ‘Have you ever thought about inviting someone else into the bedroom?' Just one time, for the sex and nothing more. I've asked her if she ever fantasises about other guys or women, but she just gets upset. She finds it offensive that I would think about inviting other people in. Jenny's never been with anybody else. If I could 'unlock' her a little bit more, maybe I could tell her the truth... but that’s never going to happen.

If she was to discover the truth, I think she'd be distraught. It was initially really hard to deal with the guilt. After that first lady, I thought, ‘My goodness what have I done? That was terrible.’ I didn’t know what to do or whether to tell her, and then things worked out ok. Then, when I found myself on the site and getting messages, I felt guilty again. But that guilt’s lessened in time, with the more experiences I’ve had.

It’s definitely benefitted our marriage

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I can see the positives it's brought to our relationship, too. It’s definitely benefitted our marriage. This is my quasi-justification... not that it can be justified. I know this isn’t normal behaviour. I’m not somebody that hits on women in bars. I’ve got no ability to chat women up, I never have done. It’s not like I go out with my mates and go over and talk to a woman. The whole ‘your wife will never find out’ kind of thing.

A secret life

There’s something quite satisfying about having a secret life. I guess that says something about my psyche as well. This is my world that nobody else knows and I can escape into it and be this type of person.

I don’t apportion any blame for my actions to Jenny. But I can see there being a case for if she’d been a bit more open minded on some things... She never really comes to the table when it comes to sex, either initiating it or talking about it. I’ve always bought her underwear or sex toys and it’s always been greeted with a look of, ‘Really?’ Perhaps I've not tried enough to keep on opening up that book. She comes from a conservative family and my attempts to try and unlock stuff has never been too successful.

Having these experiences, I’ve got a lot more confident about sex. I take a bit more control and can be in charge of what I'm doing. I know it’s disrespectful. I don’t think it’s morally justifiable. In another sense, you’ve got one life so go and have some fun.